Process for the manufacture of α, α-branched carboxylic acid vinyl esters

Patent metadata

Field	Value
Publication number	US-9783709-B2
Application number	US-201614989361-A
Country	US
Kind code	B2
Filing date	Jan 6, 2016
Priority date	Oct 10, 2013
Publication date	Oct 10, 2017
Grant date	Oct 10, 2017

Abstract

The invention relates to a process for the manufacture of α,α-branched carboxylic acids vinyl esters comprising the following steps:
isomerising and converting an olefin feed with CO and water under Koch reaction conditions to make an acid with a ratio of Non Blocking isomers (NB) versus Blocking isomers (B) of NB/B above 1.5, wherein a blocking isomer has always a tertiary carbon atom in alpha position of the carboxylic acid and in the beta position of the carboxylic acid, whereas a non-blocking isomer has primary carbon atoms in the beta position of the carboxylic acid converting the resulting acid into a vinyl ester.

First claim

What is claimed is:

1. A composition of α,α-branched carboxylic acid vinyl esters from propylene oligomers comprising:
a vinyl ester mixture derived from neo-acids, which neo-acids are derived from a propylene oligomer olefin feed having an isomer ratio of (BR1+BR2)/BR3=Ya above 20, with BR1=weight of propylene oligomer olefin with one branching alkyl group, BR2=weight of propylene oligomer olefin with two branching alkyl groups and BR3=weight of propylene oligomer olefin with three or more branching alkyl groups, wherein the neo-acids have a ratio of Non Blocking isomers (NB) versus Blocking isomers (B) of NB/B above 1.5, where the αcarbon atom is always quaternary, the carbon atom(s) in β position can either be secondary, tertiary, or quaternary, acids with a tertiary or a quaternary carbon atoms in the β position are defined as blocking isomers.

2. The composition of claim 1 wherein the propylene oligomer olefin feed is mainly a trimer of propylene or mainly a tetramer of propylene.

3. The composition of claim 1 wherein the vinyl ester mixture is derived from the reaction of the neo-acids with acetylene in presence of a zinc catalyst.

4. The composition of claim 3 , wherein the reaction has a throughput of at least 5.3 ton/hour.

5. The composition of claim 1 , wherein the neo-acid is derived from the Koch reacion of a propylene oligomer that is mainly a trimer of propylene with Ya composition.

6. A copolymer comprising the vinyl esters produced according to claim 1 .

7. The copolymer of claim 6 , wherein the copolymer comprises vinyl ester of a C10 neo-acid and vinyl acetate.

8. The composition of claim 7 wherein the C10 acid is derived from a propylene oligomer that is mainly a trimer of propylene with Ya composition.

9. The copolymer of claim 7 , wherein the copolymer comprises a 25/75 ratio of vinyl ester of the C10 neo-acid to vinyl acetate, and has a glass transition temperature of 26.5° C. or lower.

10. A polymer composition for coating, adhesive or composite applications, comprising the copolymer of claim 6 .

Assignees

• Heymans Denis
• Hexion Inc

Inventors

• Heymans Denis

Classifications

• C09J133/08

  Homopolymers or copolymers of acrylic acid esters · CPC title

• C09J133/06 Primary

  of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical · CPC title

• C09D133/08

  Homopolymers or copolymers of acrylic acid esters · CPC title

• C08F218/08

  Vinyl acetate · CPC title

• C08F18/10 Primary

  of monocarboxylic acids containing three or more carbon atoms · CPC title